2-Isopropylaniline → 4-Bromo-2-(propan-2-yl)aniline

HRID 2108592Notes

Reaction equation

HRID 2108592 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].[Br:11]Br>ClCCl>[Br:11][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:10]=1

Participants

4

Reactant 2

HCID 125612-IsopropylanilineHCID 24408Bromine

Product 1

HCID 222719374-Bromo-2-(propan-2-yl)anilineYield 135.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of 2-iso-propyl aniline (714 mg, 5.28 mmol) in dichloromethane (20 mL) at −50° C. in a dry ice/acetone bath was added a solution of bromine (269 μl, 5.28 mmol) in dichloromethane (5 mL) over 20 min. After completion of the addition, the reaction mixture was stirred for an additional hour. Purification by column chromatography (silica gel, hexane/ethyl acetate) gave 4-bromo-2-iso-propyl-phenylamine as a brown oil (1.53 g, 57%); 1H NMR (300 MHz, DMSO-d6): δ 7.01(m, 2H), 6.55(d, 1H, J=13 Hz), 5.05(bs, 2H), 2.92(m, 1H), 1.11 (d, 6H, J=7 Hz); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=Hexane/ethyl acetate [10:1]; Rf=0.11

Workup

  1. additionAfter completion of the addition
  2. customPurification by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-480a9e6070ee4c8f84d0081f25d5727a
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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